1, 4-Addition of Vinylmagnesium Bromide to α, β-Unsaturated Steroidal Ketones. I. Reaction of 16-En-20-oxo and 19-Nor-4-en-3-oxo Steroids

Abstract

The reaction of 16-en-20-oxo and 19-nor-4-en-3-oxo steroids with vinylmagnesium bromide in the presence of cupric acetate afforded 16α-vinyl-20-oxo and 19-nor-5β-vinyl-3-oxo steroids. In order to establish the configuration of vinyl group introduced by the reaction and to study the streochemical relationship between the reaction with vinylmagnesium bromide and that with a saturated Grignard reagent, some transformations of vinyl compounds derived by the reaction were undertaken. The stereochemical course of reactions was found to be identical with that of a saturated Grignard reagent.